Middleburg Vacation Packages

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Your Middleburg Vacation

With every last detail planned before you go away, our Middleburg vacation packages mean you can focus more on letting the good times roll. Whether you stay in the neighborhood of Stone Ridge, which is good for walking, or someplace else in town, this lively city promises a world of discoveries. You'll want to take in the sights during your trip to Middleburg. Carve out some time for major attractions such as Greenhill Winery & Vineyards, Cana Vineyards and Winery and Chrysalis Vineyards. A few quick clicks is all it takes to put together the ultimate Middleburg vacation on Expedia.

Top Middleburg Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD

2.5 out of 5
Price was CA $701, price is now CA $561 per person
CA $561
per person
Oct 20 - Oct 24
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
6.2/10 (1,002 reviews)
Not the nicest. Rooms were dirty and smelled

Reviewed on Jul. 5, 2025

Solomons Victorian Inn

Solomons Victorian Inn

3.5 out of 5
Price was CA $2,424, price is now CA $1,879 per person
CA $1,879
per person
Oct 10 - Oct 17
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
10/10 Exceptional! (29 reviews)
Customer service was great. Breakfast was awesome. Thanks for everything.

Reviewed on Aug. 24, 2025

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

3 out of 5
Price was CA $778, price is now CA $611 per person
CA $611
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (854 reviews)
Honestly, I didn’t see much of the property as I booked last minute due to a delayed flight. However, it was clean, exactly what I needed, and staff were kind and accommodating.

Reviewed on Aug. 27, 2025

Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
Price was CA $971, price is now CA $768 per person
CA $768
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,005 reviews)
My wife and I are repeat visitors mainly for the pool facilities. While our overall experience has been very positive our latest visit was checkered. We were given a room on the same floor as wedding party guests which was quite loud after I explicitly asked for a nonadjoining room because we are sensitive to noise. And at checkout I called several times to checkout but my calls went unanswered. So I then tried to check out via the tv option but that was unsuccessful. My last option was to stand in line to check out so overall I wasted 20 minutes for a process that should normally take 30 seconds. While these latest experiences were unfortunate I only raise them as teaching points so that improvements in efficiencies are hopefully implemented. These are easy fixes such as put guests who want peace and quiet and are paying a great deal of money on a peaceful floor away from a wedding party. Thank you

Reviewed on Aug. 24, 2025

Staybridge Suites Tysons - McLean by IHG

Staybridge Suites Tysons - McLean by IHG

3 out of 5
Price was CA $753, price is now CA $598 per person
CA $598
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.2/10 Wonderful! (1,001 reviews)
It was everything we expected.

Reviewed on Aug. 24, 2025

Ready to book your vacation to Middleburg?

 

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Middleburg Hotel Deals

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $820 per night from Sep 1 to Sep 2
CA $820
CA $1,007 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (362 reviews)
The Salamander is exquisite - the perfect stay.
"The Salamander is exquisite—luxurious and sophisticated. Its style and design are flawless, and the entire experience is top tier. You truly can’t go wrong with a stay at this beautiful resort; it’s the perfect getaway for any occasion."

Reviewed on Aug. 5, 2025

Salamander Resort And Spa
Hyatt Place Herndon Dulles Airport East

Hyatt Place Herndon Dulles Airport East

3 out of 5
13711 Sayward Blvd, Herndon, VA
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 31 to Sep 1
CA $144
CA $166 total
Aug 31 - Sep 1
includes taxes & fees
Hyatt Place Herndon Dulles Airport East
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is CA $164 per night from Sep 13 to Sep 14
CA $164
CA $189 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (1,416 reviews)
"Ok"

Reviewed on Aug. 23, 2025

Hyatt Regency Dulles
See all 965 properties in Middleburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Middleburg

Cana Vineyards and Winery

Cana Vineyards and Winery

You can enjoy a tasting or tour at Cana Vineyards and Winery during your travels to Middleburg. While in this trendy area, you can savor the top-notch restaurants.

Cana Vineyards and Winery

The Byrne Gallery

You can spend an afternoon exploring the galleries in The Byrne Gallery during your travels in Middleburg. Visit the area's spas, or simply enjoy its restaurants.

The Byrne Gallery

What to do in Middleburg

Vineyard and Winery Bus Tour from Metro DC

Vineyard and Winery Bus Tour from Metro DC

CA $151
per adult
Vineyard and Winery Bus Tour from Metro DC
See all activities in Middleburg

Frequently asked questions

How much does a Middleburg vacation package cost?
You'll find cheap prices from CA $561 on Expedia for your Middleburg escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Middleburg costs.
What are the cheapest months to go to Middleburg?
January, April and September are great times to look for cheap Middleburg vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Middleburg?
When planning your Middleburg vacation, a handful of days will be enough to see the best spots. Make sure to check out Chrysalis Vineyards — it's one of the most popular attractions in this destination. If you're after more activities, consider basing yourself here and venturing off on some day tours from Middleburg.
Is it worth booking a vacation package to Middleburg?
It's easy to see why a Middleburg vacation is on the must-do list of many travellers. Well-known attractions like Glenwood Park are just the beginning of things to keep you busy here.
How to find the best Middleburg package deals?
Landing a cheap Middleburg package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Middleburg package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Middleburg vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Middleburg vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Middleburg?
If you're planning an impromptu Middleburg vacation, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Middleburg?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Middleburg.
  2. Set a budget: Factor in costs such as flights, meals and transportation when working out how much to save for your trip to Middleburg. Then, pick a property that matches your budget, whether that's an economical stay or a lavish retreat.
  3. Decide how many days away: Start by compiling a list of the attractions you want to experience in Middleburg. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Middleburg vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.